Process and compositions for treating textiles



Patented June 25, 1946 PROCESS AND COMPOSITIONS FOR TREATING TEXTILES Glen H. Morey, Terre Haute, Ind., assignor to Commercial Solvents Corporation, Terre Haute, Ind., a corporation of Maryland N Drawing. Application December 4, 1944,

Serial No. 566,642

This invention relates to products which are suitable as assistants for the modification of textile fabrics, and more particularly to the oximes of higher alkylaminoacetones as textile "softeners to improve the softness and hand" of fabrics treated therewith.

Untreated textile fabrics have a tendency to be stiff and "boardy instead of falling in soft limp folds when draped. To impart the desired soft textural properties, called hand, to the fabric, assistants are used to treat the fabric in the washing or dyeing bath or in a subsequent operation. Such assistant, or softener must not only-impart the desired softness qualities to a range of textile materials but should also be without adverse effect on the dyeing qualities, light-fastness, etc. of the fabric, and should not readily be removed by washing and should exhibit good compatibility with other commonly used textile treating materials such as starch, gelatin, soaps, oils and the like.

I have found that the alkylaminoacetone oximes, in which the alkyl group is the residue of a higher fatty acid function well as textile softeners to impart all the desirable softness and qualities of hand and in addition have the desirable qualities mentioned above of permanence, compatibility, universality, and the like, This property is virtually lacking in the lower alkyl members.

The alkylaminoacetone oximes suitable for use as softeners in accordance with my invention have the following general formula:

H H NOH Rr-IAI--l-CHS I 1i wherein R1 is a higher alkyl radical,

Among the compounds included by this formula are decylaminoacetone oxlme; undecylaminoacetone oxlme; dodecylaminoacetone oxime; hexadecylamlnoacetone oxlme; octadecylaminoacetone oxlme, and the like.

The alkylaminoacetone oximes maybe prepared by the condensation of chloroacetone oxlme with a higher alkyl amine as described in my e pending application, Serial No. 566,641 filed as of even date herewith, and may be isolated and used as the free amine or they may be used as the hydrochloride in paste form without separation or isolation from the reaction medium, or mixtures of two or more of the oximes may be used.

A paste suitable for use in textile treating baths may conveniently be prepared according to the following procedure. I

11 Claims. (Cl. 252--s.s)

EXAMPLE I A quantity of 67 parts of octadecylamine was melted in a reaction vessel. A small amount of octadecylaminoacetone oxlme ufficient to serve as an emulsifying agent was dissolved in 250 parts of hot water and this was added to the melted octadecylamine. The solution was stirred vigorously and was allowed to cool While stirring, The small amount of octadecylaminoacetone oxlme caused'the paste to be more homogeneous than it would otherwise have been. When the paste had cooled to about 15 0., 25 parts of ethyl alcohol was stirred in, and as a result, the paste became more fluid so that it could be stirred more easily and resulted in better homogeneity. The mixture was cooled to atmospheric temperature of about 25 C. and then 30 parts of chloroacetone oxlme diluted with 25 parts of alcohol was added portionwise while stirring thoroughly for about 36 minutes. The resulting product was a smooth white paste.

The paste prepared as described in the foregoing example may be diluted with water to any desired concentration for convenience in adding to the textile bath.

Either this paste, or the pure alkylaminoacetone oxlme, as desired, is added to an aqueous treating bath of desired concentration, and either dyed or undyed fabrics are immersed therein at bath-fabric weight ratios commonly used in the art Short treating periods, as is well known for such treatments, are suflicient for immersion in the treating baths, and somewhat elevated temperatures. up to about the boiling point of water or above may advantageously be used, Agitation of the fabric during immersion is desirable to secure uniform absorption of the softener material by the fabric.

In utilizing the alkylaminoacetone oximes ac cording to my invention, I find that quantities ranging from .1% on the weight of the fabric to be treated, up to about 1% are suitable to impart the desired softness and hand to a wide variety of textile fabrics including cotton, rayon, wool, silk, and the like. The softness of the fabric increases somewhat with an increase in the amount of softener used, up to about 1%, and usually a concentration between about 0.2% and 0.5% is sufficient to impart the desired improvement to the fabric.

My softener may be used in neutral and acid treating baths at any desired concentration, and may be used in mildly alkaline baths at low concentrations, for example about .1 to 2%. At

higher concentrations the softener may il to disperse completely in the alkaline bath and upon heating may actually separate and rise to the top of the bath. However, the low concentrations mentioned above are usually sufficient to satisfacto'rily condition the fabric in alkaline baths so that the higher concentrations in alkaline media at which separation may occur, need not be encountered.

My softener is compatible with the usual textile treating agents, such as corn starch, sulfonated castor oil, polyvinyl alcohol, gelatin, soap and the like, and can be used in conjunction with any or several of them in the same bath to impart its softening properties to the fabric. When used with starch, it appears to cause the starch to exhaust onto the fabric to a greater degree than when no softener is used, and in such cases, less starch need be used to obtain the same eflects than where my softener is omitted.

Light-fastness tests show that in dyed fabrics softened with the alkylaminoacetone oximes of my invention fading is not enhanced and occurs to only about the same degree as in the untreated fabrics.

The use of my softener in conjunction with, or following the dyeing operation results in an enhanced setting of the dye of the fabrics in many cases so that if desired in these instances the softener may advantageously be used as a rinse to prevent mark-oil of printed fabrics.

The following specific examples will serve to illustrate the manner in which my oxime softeners may be utilized in accordance with my invention, but should be considered as merely illustrative and in no way limiting.

Exsuera II Aqueous treating solutions were made up in 225-ml. portions of octadecylaminoacetone oxime, and tested in comparison with two commercial textile softeners (a) the acetate of a tertiary amine (Onyxan-S) and (b) a tetraalkylammonium halide (Triton K-60) in concentrations of .l, .2, .5 and 1.0%, respectively. The various treating baths were heated to 60 C. and into each was placed a 9 inch square of cotton towelling cloth weighing approximately 15 grams each (i. e. a 15 to 1 bath)- and agitated for five minutes. The samples were removed from the .bath, squeezed to twice their original weight, dried and ironed. The hand of the treated samples were greatly improved over that of the untreated material and in every case the "hand of the fabrics treated with the cctadecylaminoacetone oxime as determined by feeling the fabric, was greatly improved over that of a similar untreated fabric and was at least equal to that of either of the two commercial softeners. the improvement increasing somewhat with each increase in the concentration of softener used.

Exsueu: III

Weighed squares of cotton fabric approximately 10" square were treated for five minutes with agitation in baths of distilled water containing 0.1, 0.2, 0.5, and 1.0%, based on the weight of the fabric, of octadecylaminoacetone oxime and in which the temperature ranged from 40 to C. and in which the weight of water in each bath was thirty timesthe weight ofthe fabric treated. A series was run under the above conditions in (a) neutral bath, (b) baths made acid with acetic acid, and (0) baths made Just alkaline to litmus with sodium hydroxide with the results that (1) The softness (as determined by feeling with 78 4 the hand) increased with increasing concentration of octadecylaminoacetone oxime.

(2) softness variation with varying concentrations was approximately equal for neutral, acid and alkaline baths.

(3) For the same concentration, the acid bath produced considerably more softness than the neutral bath and definitely more softness than the alkaline bath, that is, the softness produced by 0.1% of softener in acid bath was approximately equal to the softness produced by 0.5% softener in neutral bath, and both were approximately equal to the softness produced by 1% in the alkaline bath. l

(4) Dispersion of softener in the alkaline bat was complete at the concentrations of .1% and .2% but incomplete at the high concentrations of 0.5% and 1%.

EXAMPLE IV Sixteen squares of cotton fabric weighing approximately 15 grams each were dyed in a 20 to 1 bath containing 2% of Pontamine Blue 3BX dye by heating the bath to F., adding the cloth, heating to boiling, and boiling for one hour with frequent stirring. Fifty grams of sodium chloride were added to the dye bath and the fabric boiled therein for an additional twenty minutes. The squares were then removed from the bath, rinsed with water and dried in air.

The fabric squares so dyed were then treated in 30 to 1 baths containing, in concentrations of 0.1, 0.2, 0.5, 1.0 and 2.0% on the weight of the fabric, the following softeners (a) octadecylaminoacetone oxime, (b) the acetate of a tertiary amine (Onyxan-S) and (c) a tetraalkylammonium halide (Triton K430) respectively, the latter two being well known commercially used and acceptable softeners for comparison.

Squares were immersed in each of the softener treating baths described above, which had been brought to temperatures of 40-60 C., and the samples were allowed to remain in the baths for five minutes under frequent agitation. A dyed square was immersed in a similarly heated bath containing no softener and only distilled water for comparison. The samples were then removed, dried in air, ironed and cut in half. After treatment with softener, a portion of each softener treating bath was retained and compared as to color in order to compare the amounts of dye washed out of the sample. All baths containing softener removed less dye than the bath containing only distilled water, and the bath containing the octadecylaminoacetone oxime removed the least amount of dye for each concentration than either of the two commercial softeners indicating the dye setting effect of the new softeners which make their use as rinses for "mark of! prevention advantageous. tened sample was placed under the ultra-violet rays of a Hanovia sun lamp at a distance of 10 inches below the tubes center, and thus exposed for twenty-five minutes. sample was also similarly exposed as a check.

After exposure the samples were compared with unexposed samples, and with the exposed sample containing no softener and it was observed that, while some fading of the exposed samples had occurred, it was no greater than that suffered by the unsoftened sample in the case of the octadecylaminoacetone oxime, while one of the commercial softeners exhibited greater fading theuntreated sample.

The softness of the dyed samples was evaluated One half of each dyed, sof- A dyed, unsoftened by feeling with the hand, and the sample treated with octadecylaminoacetone oxime was found to be softer, and to have a better hand than either of the samples treated with the commercial softeners.

Exmu V Softening rayon, silk and .wool I respectively 0.2%- 0.5%, 1.0% and 2.0% on the weight of the samples treated, of each of octadecylaminoacetone oxime, the acetate of a tertiary amine (Onyxan-Sland a tetraalkylammonium halide (Triton K-60).

After treatment the samples were removed from the baths and dried. The spent baths were compared for color to evaluate the effect of the respective softeners on "mark-off prevention. This comparison showed that in the case of silk and rayon, very little dye had been removed from the sample containing the octadecylaminoacetone oxime, and that it was equal to one of the commercial softeners in this respect and superior to the other.

In the case of wool, all three softeners were equal incausing no more dye removal than that removed from the unsoftened samples.

The dyed, softened rayon samples were exposed for twenty-five minutes at inches distance from the center of a quartz ultra-violet tube, and

. at the end of the exposure, no fading was perceptible. At 5 inches from the tube some fading of allthe samples occurred.

The silk and wool samples were exposed for twenty-five minutes at 5 inches from the same a ultra-violet light source. The silk showed perceptible fading during exposure, but upon removal. from the light regained its original color. The wool thus treated showed very little initial fading and also regained its original color upon removal from the influence of the ultra-violet light, indicating that my new softener has no deleterious effect on light fastness of dyed rayon, silk and wool.

Exmu VI Treating baths were prepared containing concentrations of 0.1%, 0.2%, 0.5%, 1.0% and 2.0% each of the reaction product of chloracetone oxime and a mixture of crudehexadecylamine and octadecylamine, and the reaction product of chloroacetone oxime and a mixture of pure hexadecylamine and octadecylamine. Into these baths, made up 30 to 1 ratio on the fabric samples and temperature of 50-60 C., were immersed cotton fabric samples, and agitated for five minutes. The fabric samples were removed, squeezed to about twice their dry weight, dried in air and providing the softer results.

ironed. The feel of the samples was compared with the "feel" of an unsoi'tened blank, and with cotton fabric treated with pure octadecylaminoacetone oxime. V

Samples treated with both the crude and pure amine mixtures were appreciably softer than the unsoftened blank; the mixture of pure amines Both were somewhat inferior in softness to the pure octadecylaminoacetone oxime treated fabric, but the mixed products produced a less yellow appearance of the cloth than the pure octadecylamine product.

While the above description and examples illustrate the preferred embodiments of my invention they should not be considered limiting as departures may be made therefrom within the scope of the claims,

What is claimed is:

1. A process for improving the hand" of textile fabrics which comprises treating the fabric with an aqueous dispersion containing an alkyiaminoacetone oxime in which the alkyl group is derived from a higher fatty acid and thereafter drying the fabric.

2. A textile treating composition comprising an aqueous dispersion of an alkylaminoacetone oxime in which the alkyl group is derived from a higher fatty acid.

3. A process for improving the hand of textile fabrics, which comprises treating said fabric with an aqueous dispersion of octadecylaminoacetone oxime and thereafter drying the fabric.

4. A textile treating composition comprising octadecylaminoacetone oxime and water.

5. A textile treating agent comprising a mixture of hexadecyland octadecylaminoacetone oximes and water.

6. A textile treating composition comprising hexadecylaminoacetone oxime and water.

7. A process for improving the hand of textile fabrics which comprises treating said fabric with an aqueous dispersion of hexadecylaminoacetone oxime and thereafter drying the fabric.

8. A textile material having a soft feel obtained by impregnating with an aqueous dispersion of an alkyiaminoacetone oxime in which the alkyl groupis derived from a higher fatty acid, and thereafter drying the textile material.

9. A textile material having a soft feel obtained by impregnating with an aqueous dispersion of an octadecylaminoacetone oxime, and thereafter drying the textile material.

10. A textile material having a soft feel obtained by impregnating with. an aqueous dispersion of a hexadecylaminoacetone oxime, and thereafter drying the textile material.

11. A textile material having a soft feel obtained by. impregnating with an aqueous dispersion of a mixture of hexadecyland octadecylaminoacetone oximes, and thereafter drying the textile material.

GLEN H. MOREY. 

